U.S. patent application number 15/748799 was filed with the patent office on 2019-01-10 for plant disease control composition and plant disease control method.
This patent application is currently assigned to SUMITOMO CHEMICAL COMPANY, LIMITED. The applicant listed for this patent is SUMITOMO CHEMICAL COMPANY, LIMITED. Invention is credited to Dai HIROTOMI, So KIGUCHI.
Application Number | 20190008150 15/748799 |
Document ID | / |
Family ID | 57983763 |
Filed Date | 2019-01-10 |
![](/patent/app/20190008150/US20190008150A1-20190110-C00001.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00002.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00003.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00004.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00005.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00006.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00007.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00008.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00009.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00010.png)
![](/patent/app/20190008150/US20190008150A1-20190110-C00011.png)
View All Diagrams
United States Patent
Application |
20190008150 |
Kind Code |
A1 |
HIROTOMI; Dai ; et
al. |
January 10, 2019 |
PLANT DISEASE CONTROL COMPOSITION AND PLANT DISEASE CONTROL
METHOD
Abstract
The present invention provides a plant disease control
composition that has excellent plant disease controlling effects
and that contains a carboxamide compound represented by formula (1)
and an azole compound represented by formula (2) [wherein R.sup.1
represents a C1-6 alkyl group, R.sup.2 represents a hydrogen atom
or the like, A represents a nitrogen atom or the like, Y.sup.1
represents a halogen atom, and n represents 0 or 1]. The present
invention also provides a plant disease control method that
includes a step for treating a plant or the soil in which a plant
is being cultivated with an effective dose of the carboxamide
compound represented by formula (1) and of the azole compound
represented by formula (2). ##STR00001##
Inventors: |
HIROTOMI; Dai; (Kasai-shi,
JP) ; KIGUCHI; So; (Takarazuka-shi, JP) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
SUMITOMO CHEMICAL COMPANY, LIMITED |
Tokyo |
|
JP |
|
|
Assignee: |
SUMITOMO CHEMICAL COMPANY,
LIMITED
Tokyo
JP
|
Family ID: |
57983763 |
Appl. No.: |
15/748799 |
Filed: |
August 10, 2016 |
PCT Filed: |
August 10, 2016 |
PCT NO: |
PCT/JP2016/073634 |
371 Date: |
January 30, 2018 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
A01N 43/653 20130101;
A01N 43/50 20130101; A01N 43/56 20130101; A01N 43/56 20130101; A01N
43/653 20130101 |
International
Class: |
A01N 43/56 20060101
A01N043/56; A01N 43/50 20060101 A01N043/50; A01N 43/653 20060101
A01N043/653 |
Foreign Application Data
Date |
Code |
Application Number |
Aug 11, 2015 |
JP |
2015-158974 |
Dec 25, 2015 |
JP |
2015-253223 |
Claims
1. A composition for controlling a plant disease comprising a
carboxamide compound represented by a formula (1): ##STR00012## and
an azole compound represented by a formula (2): ##STR00013##
wherein R.sup.1 represents a C1-C6 alkyl group, R.sup.2 represents
a hydrogen atom, a C1-C3 alkyl group, a C2-C3 alkenyl group, or a
C2-C3 alkylnyl group, A represents a nitrogen atom or a methine
group, Y.sup.1 represents a halogen atom, and n is 0 or 1.
2. The composition for controlling a plant disease according to
claim 1 wherein the compound represented by the formula (2)
represents a compound represented by a formula (2a): ##STR00014##
wherein Y.sup.2 represents a chlorine atom, a fluorine atom or a
hydrogen atom.
3. The composition for controlling a plant disease according to
claim 2 wherein the compound represented by the formula (2a) is the
compound wherein Y.sup.2 represents a chlorine atom in the formula
(2a).
4. The composition for controlling a plant described in claim 1
wherein a weight ratio of the compound represented by the formula
(1) to the compound represented by the formula (2) is 1:0.0125 to
1:500.
5. A method for controlling a plant disease comprising applying
each of an effective amount of a carboxamide compound represented
by a formula (1): ##STR00015## and an azole compound represented by
a formula (2): ##STR00016## wherein R.sup.1 represents a C1-C6
alkyl group, R.sup.2 represents a hydrogen atom, a C1-C3 alkyl
group, a C2-C3 alkenyl group, or a C2-C3 alkylnyl group, A
represents a nitrogen atom or a methine group, Y.sup.1 represents a
halogen atom, and n is 0 or 1, to a plant or a soil for cultivating
the plant.
6. The method for controlling a plant disease according to claim 5
wherein the step of application to a plant or a soil for
cultivating the plant is a step of application to a seed.
7. A combined use of a carboxamide compound represented by a
formula (1): ##STR00017## and an azole compound represented by a
formula (2): ##STR00018## wherein R.sup.1 represents a C1-C6 alkyl
group, R.sup.2 represents a hydrogen atom, a C1-C3 alkyl group, a
C2-C3 alkenyl group, or a C2-C3 alkylnyl group, A represents a
nitrogen atom or a methine group, Y.sup.1 represents a halogen
atom, and n is 0 or 1.
Description
TECHNICAL FIELD
[0001] This application claims priority to and the benefit of
Japanese Patent Application Nos. 2015-158974 filed on Aug. 11, 2015
and 2015-253223 filed on Dec. 25, 2015, the entire contents of
which are incorporated herein by reference.
[0002] The present invention relates to a composition for
controlling plant diseases and a method for controlling plant
diseases.
BACKGROUND ART
[0003] Hitherto, some compounds have been known as active
ingredient for a composition for controlling plant diseases (see
Patent Documents 1 and 2).
CITATION LIST
Patent Document
[0004] Patent Document 1: WO 2011/162397 pamphlet
[0005] Patent Document 2: WO 2012/169516 pamphlet
SUMMARY OF THE INVENTION
Problems to be Solved by Invention
[0006] An object of the present invention is to provide a
composition for controlling plant diseases and a method for
controlling plant diseases, each having an excellent control
efficacy on plant disease.
Means to Solve Problems
[0007] The present inventors have intensively studied to find out a
composition for controlling plant diseases and a method for
controlling plant diseases, each having an excellent control
efficacy on plant diseases. As a result, they have found that a
composition comprising a carboxamide compound represented by the
below-mentioned formula (1) and an azole compound represented by
the below-mentioned formula (2) shows an excellent control efficacy
on plant diseases.
[0008] That is, the present invention provides the followings:
[1] A composition for controlling a plant disease comprising
[0009] a carboxamide compound represented by a formula (1):
##STR00002##
and an azole compound represented by a formula (2):
##STR00003##
wherein
[0010] R.sup.1 represents a C1-C6 alkyl group,
[0011] R.sup.2 represents a hydrogen atom, a C1-C3 alkyl group, a
C2-C3 alkenyl group, or a C2-C3 alkylnyl group,
[0012] A represents a nitrogen atom or a methine group,
[0013] Y.sup.1 represents a halogen atom, and
[0014] n is 0 or 1.
[2] The composition for controlling a plant disease described in
[1] wherein the compound represented by the formula (2) represents
a compound represented by a formula (2a):
##STR00004##
wherein
[0015] Y.sup.2 represents a chlorine atom, a fluorine atom or a
hydrogen atom.
[3] The composition for controlling a plant disease described [2]
wherein the compound represented by the formula (2a) is the
compound wherein Y.sup.2 represents a chlorine atom in the formula
(2a). [4] The composition for controlling a plant described in any
one of [1] to [3] wherein a weight ratio of the compound
represented by the formula (1) to the compound represented by the
formula (2) is 1:0.0125 to 1:500. [5] A method for controlling a
plant disease comprising applying each of an effective amount of a
carboxamide compound represented by a formula (1):
##STR00005##
and an azole compound represented by a formula (2):
##STR00006##
wherein
[0016] R.sup.1 represents a C1-C6 alkyl group,
[0017] R.sup.2 represents a hydrogen atom, a C1-C3 alkyl group, a
C2-C3 alkenyl group, or a C2-C3 alkylnyl group,
[0018] A represents a nitrogen atom or a methine group,
[0019] Y.sup.1 represents a halogen atom, and
[0020] n is 0 or 1,
to a plant or a soil for cultivating the plant. [6] The method for
controlling a plant disease described in [5] wherein the step of
application to a plant or a soil for cultivating the plant is a
step of application to a seed. [7] A combined use of a carboxamide
compound represented by a formula (1):
##STR00007##
and an azole compound represented by a formula (2):
##STR00008##
wherein
[0021] R.sup.1 represents a C1-C6 alkyl group,
[0022] R.sup.2 represents a hydrogen atom, a C1-C3 alkyl group, a
C2-C3 alkenyl group, or a C2-C3 alkylnyl group,
[0023] A represents a nitrogen atom or a methine group,
[0024] Y.sup.1 represents a halogen atom, and
[0025] n is 0 or 1.
[0026] The present invention can control plant diseases.
EMBODIMENT FOR CARRYING OUT THE INVENTION
[0027] The composition for controlling plant diseases of the
present invention (hereinafter, referred to as "present
composition") comprises the above-mentioned carboxamide compound
represented by the formula (1) (hereinafter, referred to as
"present compound 1") and the above-mentioned azole compound
represented by the formula (2) (hereinafter, referred to as
"present compound 2").
[0028] The substituent(s) as described herein is/are explained.
[0029] The expression of "C1-C3" as described herein represents
that the number of the carbon atom is from 1 to 3.
[0030] The term of "halogen atom" as described herein represents a
fluorine atom, a chlorine atom, a bromine atom, and an iodine
atom.
[0031] The term of "C1-C6 alkyl group" as described herein
represents a straight- or branched-chain saturated hydrocarbon
group having 1 to 6 of carbon atom(s), and includes, for example, a
methyl group, an ethyl group, a propyl group, an isopropyl group, a
butyl group, an isobutyl group, a sec-butyl group, a tert-butyl
group, a pentyl group, a neopentyl group, a hexyl group, and the
like. Also, the term of "C1-C3 alkyl group" as described herein
represents a straight- or branched-saturated hydrocarbon group
having 1 to 3 of carbon atom(s), and includes, for example, a
methyl group, an ethyl group, a propyl group, and an isopropyl
group.
[0032] The term of "C2-C3 alkenyl group" as described herein
represents a straight- or branched-chain unsaturated hydrocarbon
group having 2 to 3 of carbon atoms, and includes, for example, a
vinyl group, a 1-propenyl group, an isopropenyl group, and a
2-propenyl group.
[0033] The term of "C2-C3 alkynyl group" as described herein
represents a straight chain unsaturated hydrocarbon group having 2
to 3 of carbon atoms, and includes, for example, an ethynyl group,
a 1-propynyl group, and a 2-propynyl group.
[0034] First, the present compound 1 is described.
[0035] The present compound 1 includes an enantiomer. Accordingly,
the present compound 1 may include these enantiomers each singly,
or any mixture composed of these enantiomers in each an arbitrary
ratio of the respective enantiomers (for example, racemic mixture).
Specific examples of enantiomer included in the present compound 1
are shown in Table 1.
TABLE-US-00001 TABLE 1 Enantiomer Structural formula Present
compound 1-R ##STR00009## Present compound 1-S ##STR00010##
[0036] The Present compound 1 is a compound described in, for
example, WO 2011/162397 pamphlet, and may be prepared according to
a process described therein.
[0037] Next, the present compound 2 is described.
[0038] In the above-mentioned formula (2), R.sup.1 includes
preferably a C1-C4 alkyl group, more preferably a methyl group or
an ethyl group, and further preferably a methyl group.
[0039] In the above-mentioned formula (2), R.sup.2 includes
preferably a hydrogen atom, a methyl group, an ethyl group, or a
propyl group, and more preferably a methyl group.
[0040] When n is 1, the binding position of Y.sup.1 is not
particularly limited, but is preferably the position that results
in a 4-substituted benzyl group.
[0041] The present compound 2 is described, for example, in WO
2012/169516 pamphlet. The present compound 2 may be prepared
according to a known process.
[0042] Examples of the present compound 2 include the following
compounds.
[0043] A compound represented by the formula (2a):
##STR00011##
wherein
[0044] Y.sup.2 represents a chlorine atom, a fluorine atom, and a
hydrogen atom.
[0045] A compound represented by the above-mentioned formula (2a)
wherein Y.sup.2 represents a chlorine atom (hereainfter, referred
to as present compound 2-1);
[0046] A compound represented by the above-mentioned formula (2a)
wherein Y.sup.2 represents a fluorine atom (hereainfter, referred
to as present compound 2-2); and
[0047] A compound represented by the above-mentioned formula (2a)
wherein Y.sup.2 represents a hydrogen atom (hereainfter, referred
to as present compound 2-3).
[0048] Here the present compound 2 includes an enantiomer and a
diastereomer due to a configuration of organic residues that are
bounded to a cyclopentane ring. Accordingly, the present compound 2
may include these isomers each singly, or any mixture composed of
these isomers in each an arbitrary ratio of the respective isomers
(for example, racemic mixture or diastereomeric mixture). Among
them, the present compound 2 wherein a hydroxy group bounded to a
cyclopentane ring and a --R.sup.1 group are located in cis form to
each other is preferred, and the present compound 2 wherein a
hydroxy group bonded to a cyclopentane ring, a --R.sup.1 group and
a substituted or unsubstituted benzyl group are located in cis form
to one another is more preferred.
[0049] Specific examples of optical active isomers that are
included in the present compound 2 are shown in Tables 2 to 4.
TABLE-US-00002 TABLE 2 Optical Active Isomer Compound Name Present
Methyl (1R,2S,3S)-3-[(4- compound 2-4
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2R,3R)-3-[(4- compound 2-5
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2R,3R)-3-[(4- compound 2-6
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2S,3S)-3-[(4- compound 2-7
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2R,3S)-3-[(4- compound 2-8
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2S,3R)-3-[(4- compound 2-9
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2S,3R)-3-[(4- compound 2-10
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2R,3S)-3-[(4- compound 2-11
chlorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate
TABLE-US-00003 TABLE 3 Optical active isomer Compound Name Present
Methyl (1R,2S,3S)-3-[(4- compound 2-12
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2R,3R)-3-[(4- compound 2-13
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2R,3R)-3-[(4- compound 2-14
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2S,3S)-3-[(4- compound 2-15
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2R,3S)-3-[(4- compound 2-16
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2S,3R)-3-[(4- compound 2-17
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1R,2S,3R)-3-[(4- compound 2-18
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate Present
Methyl (1S,2R,3S)-3-[(4- compound 2-19
fluorophenyl)methyl]-2-hydroxy-1-methyl-2-
(1H-1,2,4-triazol-1-ylmethyl)cyclopentane carboxylate
TABLE-US-00004 TABLE 4 Optical active isomer Compound Name Present
Methyl (1R,2S,3S)-3-phenylmethyl-2-hydroxy- compound 2-20
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1S,2R,3R)-3-phenylmethyl-2-hydroxy- compound 2-21
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1R,2R,3R)-3-phenylmethyl-2-hydroxy- compound 2-22
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1S,2S,3S)-3-phenylmethyl-2-hydroxy- compound 2-23
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1R,2R,3S)-3-phenylmethyl-2-hydroxy- compound 2-24
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1S,2S,3R)-3-phenylmethyl-2-hydroxy- compound 2-25
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1R,2S,3R)-3-phenylmethyl-2-hydroxy- compound 2-26
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane carboxylate
Present Methyl (1S,2R,3S)-3-phenylmethyl-2-hydroxy- compound 2-27
1-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)cyclopentane
carboxylate
[0050] The weight ratio of the present compound 1 to the present
compound 2 in the present composition is usually 1:0.0125 to 1:500,
preferably 1:0.025 to 1:100, and more preferably 1:0.1 to 1:10.
[0051] Although the present composition may be a mixture as itself
of the present compound 1 and the present compound 2, the present
composition is usually prepared by mixing the present compound 1,
the present compound 2, and an inert carrier, and if necessary,
adding a surfactant or other pharmaceutical additives, and then
formulating into the form of oil solution, emulsifiable
concentrate, flowable formulation, wettable powder, granulated
wettable powder, dust formulation, granules and so on. Such
formulations can be used by itself or with an addition of other
inert components as an agent for controlling a plant disease.
[0052] The present composition may contain usually 0.1 to 99% by
weight, preferably 0.2 to 90% by weight, and more preferably 1 to
80% by weight of the present compound 1 and the present compound 2
in total.
[0053] Examples of an inert carrier used on the formulation include
a solid carrier and a liquid carrier, and examples of the solid
carrier include finely-divided powders or particles consisting of
minerals (for example, kaolin clay, attapulgite clay, bentonite,
montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth,
or calcite), natural organic substances (for example, corncob
powder, or walnut shell powder), synthetic organic substances (for
example, urea), salts (for example, calcium carbonate, or ammonium
sulfate), synthetic inorganic substances (for example, synthetic
hydrous silicon oxide) and so on. Examples of the liquid carrier
include aromatic hydrocarbons (for example, xylene, alkyl benzene,
or methylnaphthalene), alcohols (for example, 2-propanol, ethylene
glycol, propylene glycol, or ethylene glycol monoethyl ether),
ketones (for example, acetone, cyclohexanone, or isophorone),
vegetable oils (for example, soybean oil, or cotton oils),
petroleum-derived aliphatic hydrocarbons, esters, dimethyl
sulfoxide, acetonitrile and water.
[0054] Examples of the surfactant include anionic surfactant (for
example, alkyl sulfate salts, alkylaryl sulfonate salts, dialkyl
sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphates,
lignin sulfonate, or naphthalenesulfonate formaldehyde
polycondensation), nonionic surfactant (for example,
polyoxyethylene alkylaryl ether, polyoxyethylene alkyl
polyoxypropylene block copolymer, or sorbitan fatty acid ester) and
cationic surfactant (for example, alkyltrimethyl ammonium
salts).
[0055] Examples of the other pharmaceutical additives include
water-soluble polymer (for example, polyvinyl alcohol, or polyvinyl
pyrrolidone), polysaccharides (for example, arabic gum, alginic
acid and salts thereof, CMC (carboxymethyl-cellulose), or xanthan
gum), inorganic substances (for example, aluminum magnesium
silicate, or alumina-sol), antiseptic agent, coloring agent, and
PAP (isopropyl acid phosphate), and stabilizing agent (for example,
BHT (2,6-di-tert-butyl-4-methylphenol)).
[0056] The present composition can also be prepared by separately
formulating the present compound 1 and the present compound 2 into
different formulations according to the above-mentioned procedures,
if necessary, further diluting each of them with water, thereafter,
mixing the separately prepared different formulations comprising
the present compound 1 or the present compound 2, respectively, or
the dilute solutions thereof with each other.
[0057] The present composition may further comprise one or more
other fungicide(s) and/or insecticide(s).
[0058] The present composition can be applied to a plant or a soil
for cultivating the plant to control the plant diseases.
[0059] Examples of the plant diseases which can be controlled by
the present invention include plant diseases which are caused by a
plant pathogenic filamentous fungus or other pathogens mediated by
the plant pathogenic filamentous fungus, but are not limited
thereto.
[0060] Rice diseases: blast (Magnaporthe grisea), brown spot
(Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), and
bakanae disease (Gibberella fujikuroi);
[0061] Wheat diseases: powdery mildew (Erysiphe graminis), fusarium
blight (Fusarium graminearum, F. avenaceum, F. culmorum,
Microdochium nivale), rust (for example, yellow rust (Puccinia
striiformis), black rust (P. graminis), red rust (P. recondita)),
snow mould (Micronectriella nivale), typhula snow blight (Typhula
sp.), loose smut (Ustilago tritici), stinking smut (Tilletia
caries), eyespot (Pseudocercosporella herpotrichoides), leaf blotch
(Mycosphaerella graminicola), glume blotch (Stagonospora nodorum),
and tan spot (Pyrenophora tritici-repentis);
[0062] Barley diseases: powdery mildew (Erysiphe graminis), loose
smut (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium
nivale), rust (Puccinia striiformis, P. graminis, P. hordei), loose
smut (Ustilago nuda), scald (Rhynchosporium secalis), net blotch
(Pyrenophora teres), spot blotch (Cochliobolus sativus), leaf
stripe (Pyrenophora graminea), and damping-off caused by
rhizoctonia fungus (Rhizoctonia solani);
[0063] Corn diseases: smut (Ustilago maydis), southern leaf blight
(Cochliobolus heterostrophus), zonate leaf spot (Gloeocercospora
sorghi), southern rust (Puccinia polysora), gray leaf spot
(Cercospora zeae-maydis), and damping-off caused by rhizoctonia
fungus (Rhizoctonia solani);
[0064] Citrus diseases: melanose (Diaporthe citri), scab (Elsinoe
fawcetti), fruit rot (Penicillium digitatum, P. italicum), and
Phytophthora disease (Phytophthora parasitica, Phytophthora
citrophthora);
[0065] Apple diseases: blossom blight (Monilinia mali), canker
(Valsa ceratosperma), powdery mildew (Podosphaera leucotricha),
Alternaria leaf spot (Alternaria alternata apple pathotype), scab
(Venturia inaequalis), bitter rot (Colletotrichum acutatum), and
crown rot (Phytophtora cactorum);
[0066] Pear diseases: scab (Venturia nashicola, V. pirina), black
spot (Alternaria alternata Japanese pear pathotype), rust
(Gymnosporangium haraeanum), and Phytophthora crown and root rot
(Phytophthora cactorum);
[0067] Peach diseases: brown rot (Monilinia fructicola), scab
(Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.);
[0068] Grapes diseases: anthracnose (Elsinoe ampelina), ripe rot
(Glomerella cingulata), powdery mildew (Uncinula necator), rust
(Phakopsora ampelopsidis), black rot (Guignardia bidwellii), and
downy mildew (Plasmopara viticola);
[0069] Diseases of Japanese persimmon: anthracnose (Gloeosporium
kaki), and leaf spot (Cercospora kaki, Mycosphaerella nawae);
[0070] Diseases of Cucurbitaceae: anthracnose (Colletotrichum
lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem
blight (Mycosphaerella melonis), Fusarium wilt (Fusarium
oxysporum), downy mildew (Pseudoperonospora cubensis), Phytophthora
rot (Phytophthora sp.), and damping-off (Pythium sp.);
[0071] Tomato diseases: early blight (Alternaria solani), leaf mold
(Cladosporium fulvum), and late blight (Phytophthora
infestans);
[0072] Eggplant disease: brown spot (Phomopsis vexans), and powdery
mildew (Erysiphe cichoracearum);
[0073] Diseases of brassica family: Alternaria leaf spot
(Alternaria japonica), white spot (Cercosporella brassicae),
clubroot (Plasmodiophora brassicae), and downy mildew (Peronospora
parasitica);
[0074] welsh onion diseases: rust (Puccinia allii), and downy
mildew (Peronospora destructor);
[0075] Soybean diseases: purple stain (Cercospora kikuchii),
Sphaceloma scad (Elsinoe glycines), pod and stem blight (Diaporthe
phaseolorum var. sojae), septoria brown spot (Septoria glycines),
Cercospora leaf spot (Cercospora sojina), rust (Phakopsora
pachyrhizi), phytophthora root and stem rot (Phytophthora sojae),
damping-off caused by rhizoctonia fungus (Rhizoctonia solani),
target spot (Corynespora casiicola), and sclerotinia rot
(Sclerotinia sclerotiorum);
[0076] Kidney bean diseases: anthracnose (Colletotrichum
lindemthianum);
[0077] Peanut diseases: leaf spot (Cercospora personata), brown
leaf spot (Cercospora arachidicola), and southern blight
(Sclerotium rolfsii);
[0078] Garden pea diseases: powdery mildew (Erysiphe pisi);
[0079] Potato diseases: early blight (Alternaria solani), late
blight (Phytophthora infestans), pink rot (Phytophthora
erythroseptica), and powdery scab (Spongospora subterranean f. sp.
subterranea);
[0080] Strawberry diseases: powdery mildew (Sphaerotheca humuli),
and anthracnose (Glomerella cingulata);
[0081] Tea diseases: net blister blight (Exobasidium reticulatum),
white scab (Elsinoe leucospila), gray blight (Pestalotiopsis sp.),
and anthracnose (Colletotrichum theae-sinensis);
[0082] Tabacco diseases: brown spot (Alternaria longipes), powdery
mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum
tabacum), downy mildew (Peronospora tabacina), and black shank
(Phytophthora nicotianae);
[0083] Rape seed diseases: sclerotinia rot (Sclerotinia
sclerotiorum), and rape seed damping-off caused by Rhizoctonia
solani (Rhizoctonia solani);
[0084] Cotton diseases: cotton damping-off caused by Rhizoctonia
solani (Rhizoctonia solani);
[0085] Sugar beet diseases: cercospora leaf spot (Cercospora
beticola), leaf blight (Thanatephorus cucumeris), root rot
(Thanatephorus cucumeris), and aphanomyces root rot (Aphanomyces
cochlioides);
[0086] Rose diseases: blackspot (Diplocarpon rosae), powdery mildew
(Sphaerotheca pannosa), and downy mildew (Peronospora sparsa);
[0087] Chrysanthemum and Asteraceae vegetable diseases: downy
mildew (Bremia lactucae), leaf blight (Septoria
chrysanthemi-indici), and rust (Puccinia horiana);
[0088] Various plants diseases: diseases caused by Pythium spp.
(Pythium aphanidermatum, Pythium debarianum, Pythium graminicola,
Pythium irregulare, Pythium ultimum), Gray mold (Botrytis cinerea),
and Sclerotinia rot (Sclerotinia sclerotiorum);
[0089] Japanese radish diseases: Alternaria leaf spot (Alternaria
brassicicola);
[0090] Turfgrass diseases: dollar spot (Sclerotinia homeocarpa),
brown patch, and large patch (Rhizoctonia solani);
[0091] Banana diseases: Sigatoka disease (Mycosphaerella fijiensis,
Mycosphaerella musicola);
[0092] Sunflower diseases: downy mildew (Plasmopara halstedii);
[0093] Seed diseases or diseases in the early stages of the growth
of various plants caused by bacteria of Aspergillus spp.,
Penicillium spp., Fusarium spp., Gibberella spp., Tricoderma spp.,
Thielaviopsis spp., Rhizopus spp., Mucor spp., Corticium spp.,
Phoma spp., Rhizoctonia spp., Diplodia spp.; and
[0094] Viral diseases of various plants mediated by Polymixa genus
or Olpidium genus.
[0095] Examples of the plants to which the present composition can
be applied include the followings, but are not limited thereto.
[0096] Crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton,
soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugar cane,
and tobacco, etc.;
[0097] Vegetables: solanaceous vegetables (eggplant, tomato,
pimento, pepper, and potato, etc.), cucurbitaceous vegetables
(cucumber, pumpkin, zucchini, water melon, melon, and squash,
etc.), cruciferous vegetables (Japanese radish, white turnip,
horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard,
broccoli, and cauliflower, etc.), asteraceous vegetables (burdock,
crown daisy, artichoke, and lettuce, etc.), liliaceous vegetables
(welsh onion, onion, garlic, and asparagus), ammiaceous vegetables
(carrot, parsley, celery, and parsnip, etc.), chenopodiaceous
vegetables (spinach, and Swiss chard, etc.), lamiaceous vegetables
(perilla, mint, and basil, etc.), strawberry, sweet potato,
glutinous yam, and eddoe, etc.;
[0098] Flowers;
[0099] Foliage plants;
[0100] Turfgrass;
[0101] Fruits: pomaceous fruits (apple, pear, Japanese pear,
Chinese quince, and quince, etc.), stone fleshy fruits (peach,
plum, nectarine, Japanese apricot (Prunus mume), cherry fruit,
apricot, and prune, etc.), citrus fruits (Citrus unshiu, orange,
lemon, lime, and grapefruit, etc.) nuts (chestnuts, walnuts,
hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts,
etc.), berry fruits (blueberry, cranberry, blackberry, and
raspberry, etc.), grapes, Japanese persimmon, olive, Japanese plum,
banana, coffee, date palm, and coconuts, etc.; and
[0102] Trees other than fruit trees: tea, mulberry, flowering
plants, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo
(ginkgo biloba), lilac, maple, oak (quercus), poplar, Judas tree,
Formosan gum (Liquidambar formosana), plane tree, zelkova, Japanese
arborvitae (Thuja standishii), fir wood, hemlock, juniper, pinus,
picea, and yew (Taxus cuspidate)), etc.
[0103] The aforementioned "plant(s)" may include plants which
resistance has been imparted by genetic recombination.
[0104] Exemplary embodiments of the present composition include the
followings, but are not limited thereto.
[0105] A present composition wherein the combination of the present
compound 1 and the present compound 2 represents as follows:
[0106] a combination of the present compound 1 and the present
compound 2-1;
[0107] a combination of the present compound 1 and the present
compound 2-2:
[0108] a combination of the present compound 1 and the present
compound 2-3;
[0109] a combination of the present compound 1 and the present
compound 2-4;
[0110] a combination of the present compound 1 and the present
compound 2-5;
[0111] a combination of the present compound 1 and the present
compound 2-6;
[0112] a combination of the present compound 1 and the present
compound 2-7;
[0113] a combination of the present compound 1 and the present
compound 2-8;
[0114] a combination of the present compound 1 and the present
compound 2-9;
[0115] a combination of the present compound 1 and the present
compound 2-10;
[0116] a combination of the present compound 1 and the present
compound 2-11;
[0117] a combination of the present compound 1 and the present
compound 2-12;
[0118] a combination of the present compound 1 and the present
compound 2-13;
[0119] a combination of the present compound 1 and the present
compound 2-14;
[0120] a combination of the present compound 1 and the present
compound 2-15;
[0121] a combination of the present compound 1 and the present
compound 2-16;
[0122] a combination of the present compound 1 and the present
compound 2-17;
[0123] a combination of the present compound 1 and the present
compound 2-18;
[0124] a combination of the present compound 1 and the present
compound 2-19;
[0125] a combination of the present compound 1 and the present
compound 2-20;
[0126] a combination of the present compound 1 and the present
compound 2-21;
[0127] a combination of the present compound 1 and the present
compound 2-22;
[0128] a combination of the present compound 1 and the present
compound 2-23;
[0129] a combination of the present compound 1 and the present
compound 2-24;
[0130] a combination of the present compound 1 and the present
compound 2-25;
[0131] a combination of the present compound 1 and the present
compound 2-26;
[0132] a combination of the present compound 1 and the present
compound 2-27;
[0133] a combination of the present compound 1-R and the present
compound 2-1;
[0134] a combination of the present compound 1-R and the present
compound 2-2:
[0135] a combination of the present compound 1-R and the present
compound 2-3;
[0136] a combination of the present compound 1-R and the present
compound 2-4;
[0137] a combination of the present compound 1-R and the present
compound 2-5;
[0138] a combination of the present compound 1-R and the present
compound 2-6;
[0139] a combination of the present compound 1-R and the present
compound 2-7;
[0140] a combination of the present compound 1-R and the present
compound 2-8;
[0141] a combination of the present compound 1-R and the present
compound 2-9;
[0142] a combination of the present compound 1-R and the present
compound 2-10;
[0143] a combination of the present compound 1-R and the present
compound 2-11;
[0144] a combination of the present compound 1-R and the present
compound 2-12;
[0145] a combination of the present compound 1-R and the present
compound 2-13;
[0146] a combination of the present compound 1-R and the present
compound 2-14;
[0147] a combination of the present compound 1-R and the present
compound 2-15;
[0148] a combination of the present compound 1-R and the present
compound 2-16;
[0149] a combination of the present compound 1-R and the present
compound 2-17;
[0150] a combination of the present compound 1-R and the present
compound 2-18;
[0151] a combination of the present compound 1-R and the present
compound 2-19;
[0152] a combination of the present compound 1-R and the present
compound 2-20;
[0153] a combination of the present compound 1-R and the present
compound 2-21;
[0154] a combination of the present compound 1-R and the present
compound 2-22;
[0155] a combination of the present compound 1-R and the present
compound 2-23;
[0156] a combination of the present compound 1-R and the present
compound 2-24;
[0157] a combination of the present compound 1-R and the present
compound 2-25;
[0158] a combination of the present compound 1-R and the present
compound 2-26;
[0159] a combination of the present compound 1-R and the present
compound 2-27.
[0160] A present composition comprising the present compound 1 and
any one of the present compounds 2-1 to 2-27 wherein a weight ratio
of the present compound 1 to any one of the present compounds 2-1
to 2-27 is 1:0.0125 to 1:500;
[0161] A present composition comprising the present compound 1 and
any one of the present compounds 2-1 to 2-27 wherein a weight ratio
of the present compound 1 to any one of the present compounds 2-1
to 2-27 is 1:0.025 to 1:100;
[0162] A present composition comprising the present compound 1 and
any one of the present compounds 2-1 to 2-27 wherein a weight ratio
of the present compound 1 to any one of the present compounds 2-1
to 2-27 is 1:0.1 to 1:10;
[0163] A present composition comprising the present compound 1-R
and any one of the present compounds 2-1 to 2-27 wherein a weight
ratio of the present compound 1-R to any one of the present
compounds 2-1 to 2-27 is 1:0.0125 to 1:500;
[0164] A present composition comprising the present compound 1-R
and any one of the present compounds 2-1 to 2-27 wherein a weight
ratio of the present compound 1-R to any one of the present
compounds 2-1 to 2-27 is 1:0.025 to 1:100;
[0165] A present composition comprising the present compound 1-R
and any one of the present compounds 2-1 to 2-27 wherein a weight
ratio of the present compound 1-R to any one of the present
compounds 2-1 to 2-27 is 1:0.1 to 1:10.
[0166] The method for controlling plant diseases of the present
invention (hereinafter, referred to as "control method of the
present invention") is carried out by applying each of an effective
amount of the present compound 1 and the present compound 2, to a
plant or soil for cultivating the plant. Examples of the plant
include foliage of a plant, seeds of a plant and bulbs of a plant.
Moreover, the bulbs described herein mean discoid stems, corms,
rhizomes, tubers, tuberous, and tuberous roots.
[0167] In the control method of the present invention, the present
compound 1 and the present compound 2 may be applied separately to
a plant or soil for cultivating the plant in the same period, but
are usually applied as the present composition in terms of a
convenience on applying.
[0168] In the control method of the present invention, examples of
the method of applying the present compound 1 and the present
compound 2 include foliage treatment, soil treatment, root
treatment, and seed treatment.
[0169] Such the foliage treatment includes, for example, a method
of applying the present compound 1 and the present compound 2 onto
surface of a plant to be cultivated by a foliar application or a
stem application.
[0170] Such the soil treatment includes, for example, soil
broadcast, soil incorporation, and irrigation of the agent solution
to a soil.
[0171] Such the root treatment includes, for example, a method of
soaking a whole or a root of the plant into a medicinal solution
comprising the present compound 1 and the present compound 2, and a
method of attaching a solid formulation comprising the present
compound 1, the present compound 2 and the solid carrier to a root
of the plant.
[0172] Such the seed treatment includes, for example, an applying
of the present composition to a seed or a bulb of the plant to be
prevented from the plant disease, specifically, for example, spray
treatment by spraying a suspension of the present composition in a
mist form onto a surface of a seed or a surface of a bulb, smear
treatment by applying the wettable powder, the emulsifiable
concentrate or the flowable formulation of the present composition
with added by small amounts of water or as itself to a seed or a
bulb, immersion treatment by immersing a seed into a solution of
the present composition for a certain period of time, film-coating
treatment and pellet-coating treatment.
[0173] Each dose of the present compound 1 and the present compound
2 in the control method of the present invention may be varied
depending on a kind of plant to be treated, a kind or a frequency
of an occurrence of a plant disease as a control subject, a dosage
form, a treatment period, a treatment method, a treatment site, a
climate condition, etc. In case of an application to a foliage of
the plant or a soil for cultivating the plant, a total amount of
the present compound 1 and the present compound 2 is usually 1 to
500 g, preferably 2 to 200 g, and more preferably 10 to 100 g, per
1000 m.sup.2. Also each dose of the present compound 1 and the
present compound 2 in the treatment for seed is usually 0.001 to 10
g, and preferably 0.01 to 1 g, per 1 kg of seeds.
[0174] The emulsifiable concentrate, the wettable powder or the
flowable formulation, etc., is usually applied by diluting them
with water, and then spreading them. In this case, usually, each
concentration of the present compound 1 and the present compound 2
contain 0.0005 to 2% by weight, and preferably 0.005 to 1% by
weight of the present compound 1 and the present compound 2 in
total. The dust formulation or the granular formulation, etc., is
usually applied as itself without diluting them.
EXAMPLES
[0175] The present invention is described in more detail below by
Formulation Examples and Test Examples, but the present invention
should not be limited thereto.
[0176] First, Formulation Examples are described. Herein, "parts"
means "parts by weight".
Formulation Example 1
[0177] Five (5) parts of the present compound 1, 5 parts of any one
of the present compounds 2-1 to 2-27, 35 parts of a mixture of
white carbon and polyoxyethylene alkylether sulfate ammonium salt
(weight ratio 1:1), and 55 parts of water are mixed, and the
resultant solution is then subjected to fine grinding according to
a wet grinding method to obtain each flowable formulation.
Formulation Example 2
[0178] Five (5) parts of the present compound 1-R, 5 parts of any
one of the present compounds 2-1 to 2-27, 35 parts of a mixture of
white carbon and polyoxyethylene alkylether sulfate ammonium salt
(weight ratio 1:1), and 55 parts of water are mixed, and the
resultant solution is then subjected to fine grinding according to
a wet grinding method to obtain each flowable formulation.
Formulation Example 3
[0179] Ten (10) parts of the present compound 1, 5 parts of any one
of the present compounds 2-1 to 2-27, 1.5 parts of sorbitan
trioleate, and 28 parts of aqueous solution that contained 2 parts
of polyvinyl alcohol are mixed, and the resultant solution is then
subjected to wet fine grinding method, and thereto are added 45.50
parts of an aqueous solution that contained 0.05 parts of xanthan
gum and 0.1 part of aluminum magnesium silicate, followed by adding
10 parts of propylene glycol, and the mixture is blended by
stirring to obtain each flowable formulation.
Formulation Example 4
[0180] Ten (10) parts of the present compound 1-R, 5 parts of any
one of the present compounds 2-1 to 2-27, 1.5 parts of sorbitan
trioleate, and 28 parts of aqueous solution that contained 2 parts
of polyvinyl alcohol are mixed, and the resultant solution is then
subjected to wet fine grinding method, and thereto are added 45.50
parts of an aqueous solution that contained 0.05 parts of xanthan
gum and 0.1 part of aluminum magnesium silicate, followed by adding
10 parts of propylene glycol, and the mixture is blended by
stirring to obtain each flowable formulation.
Formulation Example 5
[0181] Five (10) parts of the present compound 1, 40 parts of any
one of the present compounds 2-1 to 2-27, 3 parts of calcium
lignosulfonate, 2 parts of sodium lauryl sulfate and 45 parts of
synthetic hydrous silicon oxide are fully ground and mixed to
obtain each wettable powder.
Formulation Example 6
[0182] Five (10) parts of the present compound 1-R, 40 parts of any
one of the present compounds 2-1 to 2-27, 3 parts of calcium
lignosulfonate, 2 parts of sodium lauryl sulfate and 45 parts of
synthetic hydrous silicon oxide are fully ground and mixed to
obtain each wettable powder.
Formulation Example 7
[0183] Five (5) parts of the present compound 1, 5 parts of any one
of the present compounds 2-1 to 2-27, 14 parts of polyoxyethylene
styryl phenyl ether, 6 parts of dodecylbenzene sulfonic acid
calcium salt, and 70 parts of xylene are mixed finely to obtain
each formulation.
Formulation Example 8
[0184] Five (5) parts of the present compound 1-R, 5 parts of any
one of the present compounds 2-1 to 2-27, 14 parts of
polyoxyethylene styryl phenyl ether, 6 parts of dodecylbenzene
sulfonic acid calcium salt, and 70 parts of xylene are mixed finely
to obtain each formulation.
[0185] Next, Test Examples are described.
Test Example 1
[0186] The present compound 1, and any one of the present compounds
2-1 to 2-27 are mixed, and each of the resultant mixtures is
diluted with dimethyl sulfoxide such that each concentration of the
present compound 1 and the present compound 2 is 10 ppm. The
resultant diluted solution is dispensed into a microtiter plate
(with 96 wells) in 1 .mu.l portion thereof. Thereto is then
dispensed 150 .mu.l of a potato dextrose broth medium (PDB medium)
to which conidia of wheat leaf blight fungus (Mycosphaerella
graminicola) is inoculated in advance. This plate is cultured at
18.degree. C. for four days, thereby allowing wheat leaf blight
fungus to undergo proliferation, and the absorbance at 550 nm of
each well of the microtiter plate is then measured to examine a
degree of growth of the wheat leaf blight fungus.
[0187] The efficacy is calculated on the basis of the obtained
degree of growth of the treated group and the untreated group,
respectively, by the below-mentioned "Equation 1". From the test
results, a high efficacy is acknowledged.
Efficacy=100.times.(X-Y)/X Equation 1
X: Degree of growth of fungus in the untreated group Y: Degree of
growth of fungus in the treated group
Test Example 2
[0188] A plastic pot is filled with soil and thereto wheat
(cultivar. Shirogane) is seeded and the plants are grown in a
greenhouse for ten days. Each of the present compound 1 and any one
of the present compounds 2-1 to 2-27 is made to a formulation
according to any of the above-mentioned Formulation Examples 1 to
8, and each of the resultant formulation is diluted with water such
that each concentration of the present compound 1 and the present
compound 2 respectively is 100 ppm. The resultant diluted solution
is sprayed to foliar parts so as to adhere adequately onto the
surfaces of leaves of the above wheats. After spraying the
dilutions, the plants are air-dried and thereto an aqueous
suspension of spores of wheat rust fungi (Puccinia recondita) is
inoculated by spraying one day after the application. After the
inoculation, the plants are placed at 27.degree. C. under humid
condition for one day, and are then cultivated under lighting for
ten to fifteen days, and a lesion area is examined (hereinafter
referred to as "treated group").
[0189] Whereas, wheats are cultivated similarly to the treated
group except that no foliage application of the above-mentioned
agent solutions are done (hereinafter referred to as "untreated
group"). A lesion area of wheat rust fungi is examined similarly to
the above-mentioned treated group.
[0190] From each of the lesion area of the treated group and the
untreated group, the efficacy of the treated group is calculated by
the following Equation 2. From the test results, a high efficacy is
acknowledged.
Efficacy=[1-(lesion area of the treated group)/(lesion area of the
untreated group)].times.100 Equation 2
Test Example 3
[0191] The present compound 1 or the present compound 2-1 was
dissolved into dimethyl sulfoxide such that each concentration of
the present compound 1 or the present compound 2-1 was adjusted to
one hundred fifty times as much as the concentration indicated in
the below-mentioned Table 5. The resultant agent solution was
dispensed into a microtiter plate (with 96 wells) in 1 .mu.l
portion thereof per well. One hundred forty nine (149) .mu.l of YBG
medium (which was prepared by dissolving 10 g of yeast extract, 10
g of Bacto Peptone, and 20 mL of glycerol into 1 L of water,
followed by sterilizing the medium) was dispensed into the wells to
which the agent solution(s) was/were dispensed. The plate was
cultivated at 18.degree. C. for six days, thereby allowing wheat
leaf blight fungus to undergo proliferation, and the absorbance at
550 nm of each well of the micro titer plate was then measured to
examine a degree of growth of the wheat leaf blight fungus
(hereinafter referred to as "treated group").
[0192] Whereas, wheat leaf blight fungus was proliferated similarly
to the case of the treated group except that dimethyl sulfoxide was
used instead of the agent solution, and the degree of the growth
was examined (hereinafter referred to as "untreated group"). The
efficacy was calculated from the respective obtained degree of
growth by the below-mentioned "Equation 1".
[0193] From the test results, it was acknowledged that a
synergistic effect was shown in the mixed-use group of the present
compound 1 and the present compound 2-1 when compared with the
single-use group of each of the above-mentioned compounds.
Efficacy (%)=100.times.(X-Y)/X Equation 1
X: Degree of growth of fungus in the untreated group Y: Degree of
growth of fungus in the treated group
TABLE-US-00005 TABLE 5 mixing ratio (Present Testing Concentration
compound 1:Present Efficacy compound in medium (ppm) compound 2-1)
(%) Present 0.1 -- 70 compound 1 Present 0.005 -- 15 compound 1
Present 0.05 -- 69 compound 2-1 Present 0.01 -- 27 compound 2-1
Present 0.1 + 0.01 1:0.1 100 compound 1 + Present compound 2-1
Present 0.005 + 0.05 1:10 100 compound 1 + Present compound 2-1
Test Example 4
[0194] Five (5) parts of the present compound 1, 35 parts of a
mixture of white carbon and ammonium polyoxyethylene alkyl ether
sulfate (the weight ratio of 1:1) and 55 parts of water were mixed,
and the mixture was then finely-ground by a wet grinding method to
obtain a flowable formulation comprising the present compound 1.
Separately, the flowable formulation comprising the present
compound 2-1 was prepared according to the above-mentioned similar
method except that the present compound 2-1 was used instead of the
present compound 1 to form a flowable formulation comprising the
present compound 2-1.
[0195] Each of the above-mentioned respective flowable
formulations, and the flowable formulation comprising the present
compound 1 and the present compound 2-1 that was prepared according
to the above-mentioned Formulation Example 3 was diluted with water
such that each concentration of the respective compounds in the
dilution solutions was adjusted to that indicated in Table 6, to
prepare the dilution solutions, respectively.
[0196] A plastic pot was filled with soil, and thereto wheat
(cultivar. Shirogane) was seeded, and the plants were grown in a
greenhouse for ten days. The above-mentioned dilution solutions
were sprayed to foliar parts so as to adhere adequately onto the
surfaces of leaves of the above wheats. After spraying the
dilutions, the plants were air-dried, and thereto an aqueous
suspension of spores of wheat rust fungus (Puccinia recondita)
spores was inoculated by spraying one day after the application.
After the inoculation, the plants were placed at 23.degree. C.
under humid condition for one day, and are then cultivated at
23.degree. C. under lighting for ten days, and a lesion area was
examined (hereinafter referred to as "lesion area of the treated
group").
[0197] Whereas, wheats were cultivated similarly to the treated
group except that no foliage application of the above-mentioned
agent solutions were done, and the wheat red rust fungus (Puccinia
recondita) were inoculated, and the lesion area thereof was
examined (hereinafter referred to as "lesion area of the untreated
group").
[0198] From each of the lesion area of the treated group and the
untreated group, respectively, the efficacy of the treated group
was calculated by the below-mentioned Equation 2.
[0199] From the test results, it was acknowledged that a
synergistic effect was shown in the mixed-use group of the present
compound 1 and the present compound 2-1 when compared with the
single-use group of each of the above-mentioned compounds.
Efficacy (%)=[1-(lesion area of the treated group)/(lesion area of
the untreated group)].times.100 Equation 2
TABLE-US-00006 TABLE 6 mixing ratio (Present Testing Concentration
compound 1:Present Efficacy compound in medium (ppm) compound 2-1)
(%) Present 0.01 -- 68 compound 1 Present 0.0005 -- 56 compound 1
Present 0.005 -- 51 compound 2-1 Present 0.001 -- 44 compound 2-1
Present 0.01 + 0.001 1:0.1 100 compound 1 + Present compound 2-1
Present 0.0005 + 0.005 1:10 100 compound 1 + Present compound
2-1
* * * * *